A 4-nitroimidazole compound represented by the following general formula (1):
wherein X2 represents a chlorine atom or bromine atom, is useful as a synthetic intermediate used for producing various pharmaceuticals and agricultural chemicals, and particularly used for producing antitubercular agents.
For example, methods represented by the following Reaction scheme-1 and -2 have previously been known as methods for producing the 4-nitroimidazole compound represented by general formula (1) (Jerzy Suwinski, Ewa Salwinska, Jan Watras, and Maria Widel, Polish Journal of Chemistry, 56, 1261-1272 (1982)).

wherein XA represents a halogen atom.
However, these methods have various disadvantages, and thus, are not adequate as production methods that are industrially applied.
For example, in the method represented by Reaction scheme-1, compounds (6) and (7) that are reaction intermediates are chemically unstable, and there is a risk that these compounds may explode due to impacts such as fall or friction. In addition, in this method, the temperature applied during the reaction to obtain the compound (7) from the compound (6) by heating (approximately 130° C.) exceeds the TNR (Temperature of No Return; the maximal temperature ranging from 60° C. to 70° C., at which the compound can safely be handled in a chemical processing apparatus) of the compound (6). Thus, it has been extremely dangerous to industrially produce the compound of interest in high volume by this method.
The method represented by Reaction scheme-2 involves a reaction of nitrating the compound (8). However, the compound (1a) can be obtained only at low yield by such nitration, and thus, this method is industrially disadvantageous.